data_GCK
# 
_chem_comp.id                                    GCK 
_chem_comp.name                                  
;PHOSPHORIC ACID 9-(2-GUANIDINOETHOXY-3-(2-DEOXY-BETA-D-ERYTHROPENTOFURANOSYL))-3H-PYRIMIDO-[5,4-B][1,4]-BENZOOXAZIN-2-ONE]-5'-ESTER
;
_chem_comp.type                                  "DNA LINKING" 
_chem_comp.pdbx_type                             ATOMN 
_chem_comp.formula                               "C18 H24 N6 O9 P" 
_chem_comp.mon_nstd_parent_comp_id               DC 
_chem_comp.pdbx_synonyms                         ? 
_chem_comp.pdbx_formal_charge                    1 
_chem_comp.pdbx_initial_date                     2001-12-07 
_chem_comp.pdbx_modified_date                    2009-01-07 
_chem_comp.pdbx_ambiguous_flag                   N 
_chem_comp.pdbx_release_status                   REL 
_chem_comp.pdbx_replaced_by                      ? 
_chem_comp.pdbx_replaces                         ? 
_chem_comp.formula_weight                        499.392 
_chem_comp.one_letter_code                       C 
_chem_comp.three_letter_code                     GCK 
_chem_comp.pdbx_model_coordinates_details        ? 
_chem_comp.pdbx_model_coordinates_missing_flag   N 
_chem_comp.pdbx_ideal_coordinates_details        "OpenEye OEToolkits" 
_chem_comp.pdbx_ideal_coordinates_missing_flag   N 
_chem_comp.pdbx_model_coordinates_db_code        1KGK 
_chem_comp.pdbx_subcomponent_list                ? 
_chem_comp.pdbx_processing_site                  RCSB 
# 
loop_
_chem_comp_atom.comp_id 
_chem_comp_atom.atom_id 
_chem_comp_atom.alt_atom_id 
_chem_comp_atom.type_symbol 
_chem_comp_atom.charge 
_chem_comp_atom.pdbx_align 
_chem_comp_atom.pdbx_aromatic_flag 
_chem_comp_atom.pdbx_leaving_atom_flag 
_chem_comp_atom.pdbx_stereo_config 
_chem_comp_atom.model_Cartn_x 
_chem_comp_atom.model_Cartn_y 
_chem_comp_atom.model_Cartn_z 
_chem_comp_atom.pdbx_model_Cartn_x_ideal 
_chem_comp_atom.pdbx_model_Cartn_y_ideal 
_chem_comp_atom.pdbx_model_Cartn_z_ideal 
_chem_comp_atom.pdbx_component_atom_id 
_chem_comp_atom.pdbx_component_comp_id 
_chem_comp_atom.pdbx_ordinal 
GCK P      P    P 0 1 N N N 7.662  -5.129 20.482 -4.060 -1.522  2.845  P      GCK 1  
GCK O1P    O1P  O 0 1 N N N 6.944  -6.421 20.811 -4.581 -2.443  3.910  O1P    GCK 2  
GCK O2P    O2P  O 0 1 N N N 7.615  -4.555 19.136 -3.944 -2.170  1.368  O2P    GCK 3  
GCK "O5'"  O5*  O 0 1 N N N 7.085  -4.026 21.449 -2.581 -0.926  3.121  "O5'"  GCK 4  
GCK N1     N1   N 0 1 N N N 7.515  -0.140 22.319 1.164  -2.047  0.989  N1     GCK 5  
GCK C6     C6   C 0 1 N N N 7.976  -0.856 21.258 -0.007 -2.763  0.884  C6     GCK 6  
GCK C2     C2   C 0 1 N N N 7.583  1.244  22.321 2.366  -2.541  0.452  C2     GCK 7  
GCK O2     O2   O 0 1 N N N 7.135  1.839  23.285 3.421  -1.911  0.541  O2     GCK 8  
GCK N3     N3   N 0 1 N N N 8.146  1.895  21.267 2.341  -3.769  -0.187 N3     GCK 9  
GCK C4     C4   C 0 1 N N N 8.602  1.190  20.231 1.231  -4.450  -0.288 C4     GCK 10 
GCK N4     N4   N 0 1 N N N 9.182  1.829  19.206 1.209  -5.672  -0.924 N4     GCK 11 
GCK C5     C5   C 0 1 N N N 8.529  -0.237 20.192 -0.055 -3.947  0.274  C5     GCK 12 
GCK O8     O8   O 0 1 N N N 8.965  -0.986 19.126 -1.223 -4.678  0.160  O8     GCK 13 
GCK C9     C9   C 0 1 Y N N 9.567  -0.316 18.129 -1.168 -5.893  -0.490 C9     GCK 14 
GCK C10    C10  C 0 1 Y N N 10.066 -1.079 17.074 -2.363 -6.608  -0.590 C10    GCK 15 
GCK C11    C11  C 0 1 Y N N 10.646 -0.423 16.002 -2.377 -7.843  -1.236 C11    GCK 16 
GCK C12    C12  C 0 1 Y N N 10.763 0.970  15.962 -1.201 -8.360  -1.779 C12    GCK 17 
GCK C13    C13  C 0 1 Y N N 10.294 1.738  17.017 -0.007 -7.644  -1.679 C13    GCK 18 
GCK C14    C14  C 0 1 Y N N 9.693  1.065  18.098 0.021  -6.403  -1.033 C14    GCK 19 
GCK O15    O15  O 0 1 N N N 10.353 3.103  17.152 1.128  -8.172  -2.219 O15    GCK 20 
GCK C16    C16  C 0 1 N N N 11.703 3.674  16.653 0.971  -9.014  -3.359 C16    GCK 21 
GCK C17    C17  C 0 1 N N N 12.166 4.717  17.565 2.206  -8.913  -4.234 C17    GCK 22 
GCK N18    N18  N 0 1 N N N 11.234 5.796  17.729 2.367  -7.519  -4.708 N18    GCK 23 
GCK C19    C19  C 0 1 N N N 11.338 6.980  17.077 3.419  -7.146  -5.529 C19    GCK 24 
GCK N20    N20  N 0 1 N N N 10.525 7.939  17.305 3.581  -5.841  -5.982 N20    GCK 25 
GCK N21    N21  N 1 1 N N N 12.256 7.117  16.064 4.341  -8.115  -5.910 N21    GCK 26 
GCK "C2'"  C2*  C 0 1 N N N 5.471  -0.906 23.595 0.790  0.372   0.733  "C2'"  GCK 27 
GCK "C5'"  C5*  C 0 1 N N N 6.840  -4.327 22.834 -2.017 -0.048  2.160  "C5'"  GCK 28 
GCK "C4'"  C4*  C 0 1 N N R 6.409  -3.052 23.558 -0.634 0.377   2.635  "C4'"  GCK 29 
GCK "O4'"  O4*  O 0 1 N N N 7.538  -2.150 23.588 0.189  -0.803  2.715  "O4'"  GCK 30 
GCK "C1'"  C1*  C 0 1 N N R 6.827  -0.764 23.554 1.157  -0.778  1.657  "C1'"  GCK 31 
GCK "C3'"  C3*  C 0 1 N N S 5.266  -2.244 22.953 0.064  1.317   1.662  "C3'"  GCK 32 
GCK "O3'"  O3*  O 0 1 N N N 3.958  -2.848 23.212 1.008  2.125   2.360  "O3'"  GCK 33 
GCK O3P    O3P  O 0 1 N Y N 9.117  -5.348 20.931 -4.945 -0.191  2.600  O3P    GCK 34 
GCK HOP2   2HOP H 0 0 N N N 8.065  -3.744 18.930 -4.712 -2.660  1.004  HOP2   GCK 35 
GCK H6     H6   H 0 1 N N N 7.910  -1.784 21.266 -0.892 -2.316  1.324  H6     GCK 36 
GCK H4     H4   H 0 1 N N N 9.249  2.687  19.210 2.053  -6.066  -1.323 H4     GCK 37 
GCK H10    H10  H 0 1 N N N 10.011 -2.007 17.090 -3.282 -6.209  -0.169 H10    GCK 38 
GCK H11    H11  H 0 1 N N N 10.967 -0.924 15.287 -3.304 -8.403  -1.316 H11    GCK 39 
GCK H12    H12  H 0 1 N N N 11.156 1.381  15.227 -1.221 -9.324  -2.282 H12    GCK 40 
GCK H161   1H16 H 0 0 N N N 12.362 2.963  16.607 0.846  -10.042 -3.004 H161   GCK 41 
GCK H162   2H16 H 0 0 N N N 11.593 4.043  15.763 0.068  -8.710  -3.899 H162   GCK 42 
GCK H171   1H17 H 0 0 N N N 12.340 4.319  18.432 3.109  -9.193  -3.682 H171   GCK 43 
GCK H172   2H17 H 0 0 N N N 13.004 5.075  17.231 2.107  -9.562  -5.110 H172   GCK 44 
GCK H18    H18  H 0 1 N N N 10.574 5.685  18.269 1.689  -6.830  -4.421 H18    GCK 45 
GCK H201   1H20 H 0 0 N N N 9.895  7.840  17.882 4.361  -5.590  -6.585 H201   GCK 46 
GCK H202   2H20 H 0 0 N N N 10.608 8.682  16.881 2.934  -5.099  -5.727 H202   GCK 47 
GCK H211   1H21 H 0 0 N N N 12.276 7.839  15.597 4.252  -9.079  -5.597 H211   GCK 48 
GCK H212   2H21 H 0 0 N N N 12.811 6.481  15.897 5.128  -7.886  -6.512 H212   GCK 49 
GCK "H2'1" 1H2* H 0 0 N N N 5.028  -0.204 23.093 0.107  0.030   -0.055 "H2'1" GCK 50 
GCK "H2'2" 2H2* H 0 0 N N N 5.143  -0.900 24.508 1.674  0.806   0.256  "H2'2" GCK 51 
GCK "H5'1" 1H5* H 0 0 N N N 7.646  -4.680 23.242 -1.946 -0.568  1.202  "H5'1" GCK 52 
GCK "H5'2" 2H5* H 0 0 N N N 6.143  -4.997 22.906 -2.666 0.824   2.052  "H5'2" GCK 53 
GCK "H4'"  H4*  H 0 1 N N N 6.172  -3.284 24.480 -0.708 0.804   3.640  "H4'"  GCK 54 
GCK "H1'"  H1*  H 0 1 N N N 7.105  -0.259 24.347 2.145  -0.631  2.106  "H1'"  GCK 55 
GCK "H3'"  H3*  H 0 1 N N N 5.400  -2.165 21.985 -0.622 1.992   1.141  "H3'"  GCK 56 
GCK H3T    H3T  H 0 1 N Y N 3.828  -3.696 22.805 0.752  3.054   2.222  H3T    GCK 57 
GCK HOP3   3HOP H 0 0 N N N 9.681  -5.393 20.168 -5.917 -0.279  2.499  HOP3   GCK 58 
# 
loop_
_chem_comp_bond.comp_id 
_chem_comp_bond.atom_id_1 
_chem_comp_bond.atom_id_2 
_chem_comp_bond.value_order 
_chem_comp_bond.pdbx_aromatic_flag 
_chem_comp_bond.pdbx_stereo_config 
_chem_comp_bond.pdbx_ordinal 
GCK P     O1P    DOUB N N 1  
GCK P     O2P    SING N N 2  
GCK P     "O5'"  SING N N 3  
GCK P     O3P    SING N N 4  
GCK O2P   HOP2   SING N N 5  
GCK "O5'" "C5'"  SING N N 6  
GCK N1    C6     SING N N 7  
GCK N1    C2     SING N N 8  
GCK N1    "C1'"  SING N N 9  
GCK C6    C5     DOUB N N 10 
GCK C6    H6     SING N N 11 
GCK C2    O2     DOUB N N 12 
GCK C2    N3     SING N N 13 
GCK N3    C4     DOUB N N 14 
GCK C4    N4     SING N N 15 
GCK C4    C5     SING N N 16 
GCK N4    C14    SING N N 17 
GCK N4    H4     SING N N 18 
GCK C5    O8     SING N N 19 
GCK O8    C9     SING N N 20 
GCK C9    C10    DOUB Y N 21 
GCK C9    C14    SING Y N 22 
GCK C10   C11    SING Y N 23 
GCK C10   H10    SING N N 24 
GCK C11   C12    DOUB Y N 25 
GCK C11   H11    SING N N 26 
GCK C12   C13    SING Y N 27 
GCK C12   H12    SING N N 28 
GCK C13   C14    DOUB Y N 29 
GCK C13   O15    SING N N 30 
GCK O15   C16    SING N N 31 
GCK C16   C17    SING N N 32 
GCK C16   H161   SING N N 33 
GCK C16   H162   SING N N 34 
GCK C17   N18    SING N N 35 
GCK C17   H171   SING N N 36 
GCK C17   H172   SING N N 37 
GCK N18   C19    SING N N 38 
GCK N18   H18    SING N N 39 
GCK C19   N20    SING N N 40 
GCK C19   N21    DOUB N N 41 
GCK N20   H201   SING N N 42 
GCK N20   H202   SING N N 43 
GCK N21   H211   SING N N 44 
GCK N21   H212   SING N N 45 
GCK "C2'" "C1'"  SING N N 46 
GCK "C2'" "C3'"  SING N N 47 
GCK "C2'" "H2'1" SING N N 48 
GCK "C2'" "H2'2" SING N N 49 
GCK "C5'" "C4'"  SING N N 50 
GCK "C5'" "H5'1" SING N N 51 
GCK "C5'" "H5'2" SING N N 52 
GCK "C4'" "O4'"  SING N N 53 
GCK "C4'" "C3'"  SING N N 54 
GCK "C4'" "H4'"  SING N N 55 
GCK "O4'" "C1'"  SING N N 56 
GCK "C1'" "H1'"  SING N N 57 
GCK "C3'" "O3'"  SING N N 58 
GCK "C3'" "H3'"  SING N N 59 
GCK "O3'" H3T    SING N N 60 
GCK O3P   HOP3   SING N N 61 
# 
loop_
_pdbx_chem_comp_descriptor.comp_id 
_pdbx_chem_comp_descriptor.type 
_pdbx_chem_comp_descriptor.program 
_pdbx_chem_comp_descriptor.program_version 
_pdbx_chem_comp_descriptor.descriptor 
GCK SMILES           ACDLabs              10.04 "O=C3N=C2C(Oc1cccc(OCCNC(=[NH2+])\N)c1N2)=CN3C4OC(C(O)C4)COP(=O)(O)O" 
GCK InChI            InChI                1.02b 
"InChI=1/C18H23N6O9P/c19-17(20)21-4-5-30-10-2-1-3-11-15(10)22-16-12(32-11)7-24(18(26)23-16)14-6-9(25)13(33-14)8-31-34(27,28)29/h1-3,7,9,13-14,25H,4-6,8H2,(H4,19,20,21)(H,22,23,26)(H2,27,28,29)/p+1/t9-,13+,14+/m0/s1/fC18H24N6O9P/h21-22,27-28H,19-20H2/q+1" 
GCK InChIKey         InChI                1.02b GCBWWBGDWVGEAS-RGLIBAEWDV 
GCK SMILES_CANONICAL CACTVS               3.341 "NC(=[NH2+])NCCOc1cccc2OC3=CN([C@H]4C[C@H](O)[C@@H](CO[P](O)(O)=O)O4)C(=O)N=C3Nc12" 
GCK SMILES           CACTVS               3.341 "NC(=[NH2+])NCCOc1cccc2OC3=CN([CH]4C[CH](O)[CH](CO[P](O)(O)=O)O4)C(=O)N=C3Nc12" 
GCK SMILES_CANONICAL "OpenEye OEToolkits" 1.5.0 "c1cc2c(c(c1)OCCNC(=[NH2+])N)NC3=NC(=O)N(C=C3O2)[C@H]4C[C@@H]([C@H](O4)COP(=O)(O)O)O" 
GCK SMILES           "OpenEye OEToolkits" 1.5.0 "c1cc2c(c(c1)OCCNC(=[NH2+])N)NC3=NC(=O)N(C=C3O2)C4CC(C(O4)COP(=O)(O)O)O" 
# 
loop_
_pdbx_chem_comp_identifier.comp_id 
_pdbx_chem_comp_identifier.type 
_pdbx_chem_comp_identifier.program 
_pdbx_chem_comp_identifier.program_version 
_pdbx_chem_comp_identifier.identifier 
GCK "SYSTEMATIC NAME" ACDLabs              10.04 "9-(2-{[amino(iminio)methyl]amino}ethoxy)-3-(2-deoxy-5-O-phosphono-beta-D-erythro-pentofuranosyl)-3H-pyrimido[5,4-b][1,4]benzoxazin-2(10H)-one"           
GCK "SYSTEMATIC NAME" "OpenEye OEToolkits" 1.5.0 "[amino-[2-[[3-[(2R,4S,5R)-4-hydroxy-5-(phosphonooxymethyl)oxolan-2-yl]-2-oxo-10H-pyrimido[5,4-b][1,4]benzoxazin-9-yl]oxy]ethylamino]methylidene]azanium" 
# 
